TY - JOUR
T1 - Novel metabolic pathway of phenols catalyzed by cytochrome P450 and its mechanism
AU - Mashino, Tadahiko
N1 - Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2000/12
Y1 - 2000/12
N2 - We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types: the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.
AB - We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types: the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.
KW - Cytochrome P450
KW - Cytochrome P450 model
KW - Dibenzodioxin
KW - Drug metabolism
KW - Estrogen
KW - Phenol coupling
KW - Phenol metabolism
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U2 - 10.5059/yukigoseikyokaishi.58.1202
DO - 10.5059/yukigoseikyokaishi.58.1202
M3 - Article
AN - SCOPUS:21144437856
VL - 58
SP - 1202
EP - 1209
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 12
ER -